Triphenylphosphine → 11-Ethyl-5,11-dihydro-8-{2-[4-(5-formyl-2-furanyl)-2-methylphenoxy]ethyl}-5-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 393276Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:15]([N:17]1[C:23]2[N:24]=[CH:25][C:26]([CH2:28][CH2:29][OH:30])=[CH:27][C:22]=2[C:21](=[O:31])[N:20]([CH3:32])[C:19]2[CH:33]=[CH:34][CH:35]=[N:36][C:18]1=2)[CH3:16].O[C:38]1[CH:43]=[CH:42][C:41]([C:44]2[O:48][C:47]([CH:49]=[O:50])=[CH:46][CH:45]=2)=[CH:40][C:39]=1[CH3:51].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH2:15]([N:17]1[C:23]2[N:24]=[CH:25][C:26]([CH2:28][CH2:29][O:30][C:38]3[CH:43]=[CH:42][C:41]([C:44]4[O:48][C:47]([CH:49]=[O:50])=[CH:46][CH:45]=4)=[CH:40][C:39]=3[CH3:51])=[CH:27][C:22]=2[C:21](=[O:31])[N:20]([CH3:32])[C:19]2[CH:33]=[CH:34][CH:35]=[N:36][C:18]1=2)[CH3:16]

Participants

Conditions

Temperature: 25 °C

Procedure

DIAD (107 μL, 0.54 mmol) was added dropwise to a solution of 11-ethyl-5,11-dihydro-8-(2-hydroxyethyl)-5-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (135 mg, 0.45 mmol), 5-(4-hydroxy-3-methylphenyl)-2-furanecarboxaldehyde (110 mg, 0.54 mmol) and PPh3 (143 mg, 0.54 mmol) in THF (4 mL) at 25° C. The reaction mixture was stirred at 25° C. for 18 h. The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 3:2) to give the title compound (147 mg, 67% yield) as a pale yellow foam.

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by flash chromatography (Hexane:EtOAc, 3:2)

Sources & evidence

ORD record: ord-b95bbfecdedb4ebd9502211117b41ac7
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806265B2

Reaction notes

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